2-(2-aminothiazol-4-yl)-2-[(Z)-methoxyimino]acetic acid-2-benzothiazolylthioester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(2-aminothiazol-4-yl)-2-[(Z)-methoxyimino]acetic acid-2-benzothiazolylthioester
• 英文别名: (Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetic acid 2-benzthiazolyl thioester；2-(2-aminothiazol-4-yl)-(Z)-2-methoxyimino-acetic acid 2-benzothiazolyl thioester；2-(2-amino-4-thiazolyl)-2-(Z)-methoxyimino-acetic acid 2-benzthiazolyl thioester；2-(2-amino-4-thiazolyl)-2-(Z)-methoxyimino-acetic acid-2-benzthiazolyl thioester；2-(2-aminothiazol-4-yl)-2-(Z)-methoxylimino-acetic acid 2-benzthiazolylthioester；1,3-benzothiazol-2-ylsulfanyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate
• 化学式: C₁₃H₁₀N₄O₃S₃
• 分子量: 366.445
• InChiKey: RGIOMRCRPCPYTP-YVLHZVERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  182
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(2-aminothiazol-4-yl)-2-[(Z)-methoxyimino]acetic acid-2-benzothiazolylthioester 、 特戊酸碘甲酯 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 正己烷 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 生成 7-[2-(2-amino-4-thiazolyl)-2-(Z)-methoxyimino-acetamido]-3-methyl-3-cephem-4-carboxylic acid pivaloyloxymethyl ester hydrochloride
  参考文献：
  名称：

  Process for manufacturing cephalosporin esters

  摘要：

  头孢菌素酯的结构式为##STR1##其中R.sup.2为氢或酰基，R.sup.1为易于水解去除的基团，以及公认的药用酸盐。根据公式I中R.sup.2为酰基的碱性化合物，可通过将7-氨基-3-甲基-3-头孢烯-4-羧酸（7-ADCA）与公式为##STR2##的双环亚胺在部分氯化的较低烷烃中反应，其中n为整数3、4或5，以及公式为X--R.sup.1 III的卤化物，其中X为卤素，R.sup.1具有上述意义，如果需要的话，处理公式I中R.sup.2为氢的所得化合物与未保护或可选择保护的酰化试剂，剥离可能存在的保护基团，并且如果需要的话，将公式I中R.sup.2为酰基的所得碱性化合物转化为药用酸盐。

  公开号：

  US04716227A1
• 作为产物：
  描述：

  氨噻肟酸 、 二硫化二苯并噻唑 在 三苯基膦 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 2-(2-aminothiazol-4-yl)-2-[(Z)-methoxyimino]acetic acid-2-benzothiazolylthioester
  参考文献：
  名称：

  .beta.-Lactams

  摘要：

  提供了光学均匀的β-内酰胺，其结构式如下：其中Z是易于水解的酰基，R.sup.1是氨基或可转化为氨基的基团，R.sup.2是氢或易于水解的保护基团，R.sup.3和R.sup.4分别是低碳氢基团，可选地含氧，并通过碳原子连接，这些基团也可以相互连接形成环，但R.sup.1是易于水解的酰胺基团当R.sup.2为氢时，以及相应的光学对映体，它们的制造和用于制造抗微生物活性的β-内酰胺以及在其制造中可用的新型中间体。

  公开号：

  US04576751A1

文献信息

• Process for the manufacture of 1-sulpho-2-oxoazetidine carboxylic acid
  申请人：Hoffmann-La Roche Inc.

  公开号：US04652651A1

  公开（公告）日：1987-03-24

  The manufacture of 1-sulpho-2-oxazetidine derivatives of the formula ##STR1## in which Het is an optionally amino-substituted, 5- or 6-membered, aromatic heterocycle containing 1 or 2 nitrogen atoms and optionally also an oxygen or sulphur atom, R.sup.1 is hydrogen, lower alkyl, phenyl-lower alkyl, lower alkanoyl, lower alkoxycarbonyl, lower alkenyl-lower alkyl, lower alkoxycarbonyl-lower alkyl, phenyl-lower-alkoxycarbonyl-lower alkyl, nitrophenyl-lower-alkoxycarbonyl-lower alkyl or carboxy-lower alkyl and R.sup.2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxycarbonyl, lower alkanoyloxy-lower alkyl, lower alkoxycarbonyl-lower alkenyl, hydroxyiminomethyl, lower alkoxyiminomethyl, carbamoyl, carbamoyl-lower alkenyl or carbamoyloxy-lower alkyl, the group .dbd.NOR.sup.1 being present at least partially in the syn-form, in racemic form or in the form of the 3S-enantiomer, and of readily hydrolyzable esters and pharmaceutically compatible salts of these compounds, by acylating a compound of the formula ##STR2## in which R.sup.20 equals R.sup.2 or can also represent a 2,2-dimethyl-1,3-dioxolan-4-yl group and R.sup.3 is hydrogen or sulpho, or a salt thereof with a thioester of the formula ##STR3## in which Het is as above and R.sup.10 has any of the values of R.sup.1 except carboxy-lower alkyl, and can also represent a tri-lower alkyl-silyl-lower-alkoxycarbonyl-lower alkyl group or a carboxy-lower alkyl group converted into a readily hydrolyzable ester group, and the group .dbd.NOR.sup.10 is present at least partially in the syn-form, and carrying out subsequent steps (N-sulphonation, conversion of R.sup.20 into R.sup.2, R.sup.10 into R.sup.1), some of which are optional. The invention also provides certain novel products of formula I and benzthiazolyl thioesters of formula III per se and the preparation of the benzthiazolyl thioesters by esterifying corresponding carboxylic acids. Finally, the invention provides a process for the preparation of carboxylic acids in which R.sup.1 is t-alkoxycarbonylmethyl. The compounds of formula I have antimicrobial activity.

  该专利描述了一种制备1-磺酸-2-噁唑环丙烷衍生物的方法，其化学式为##STR1##其中Het是一个含有1或2个氮原子和可能还有一个氧原子或硫原子的可选氨基取代的5或6元芳香杂环，R.sup.1是氢、低烷基、苯基-低烷基、低烷酰、低烷氧羰基、低烯基-低烷基、低烷氧羰基-低烷基、苯基-低烷氧羰基-低烷基、硝基苯基-低烷氧羰基-低烷基或羧基-低烷基，R.sup.2是氢、低烷基、低烯基、低炔基、低烷氧羰基、低烷酰氧基-低烷基、低烷氧羰基-低烯基、羟基亚胺甲基、低烷氧亚胺甲基、氨甲酰基、氨甲酰基-低烯基或氨甲酰氧基-低烷基，.dbd.NOR.sup.1基团至少部分以syn-形式存在，是外消旋形式或3S-对映体形式，以及这些化合物的易水解酯和药用兼容盐的制备方法。
• Cephalosporin derivatives
  申请人：Sankei Pharmaceutical Co., Ltd.

  公开号：US04987129A1

  公开（公告）日：1991-01-22

  There are disclosed a .beta.-lactam compound represented by the formula (I): ##STR1## wherein R.sub.1 represents an acyl group; M represents a hydrogen atom, a protective group or an eliminatable group which is easily hydrolyzable in a human body; B represents a group represented by the formula (b): ##STR2## where at least one of R.sub.2, R.sub.3 and R.sub.9 represent a group represented by the formula: --A--OR.sub.4 where R.sub.4 represents a hydrogen or a lower alkyl group; and A represents a straight or branched alkylene group having 1 to 6 carbon atoms; and a remaining group or groups are each independently a hydrogen atom; a cyano group; a lower alkyl group which may be substituted by a halogen atom; a carbamoyl group which may be substituted by a lower alkyl group; a cycloalkyl group; or a carboxyl group which may be substituted by a protective group or an eliminatable group which is easily hydrolyzable in a human body, and also when R.sub.9 is --A--OR.sub.4, and R.sub.3 may be combined with each other to form an alkylene group having 3 to 4 carbon atoms; and Z represents a nitrogen atom or a group represented by the formula: C--R.sub.10 where R.sub.10 represents a hydrogen atom, a carboxyl group or a lower alkyl group which may be substituted by a hydroxy group or a lower alkoxy group, or its pharmaceutically acceptable salt, and a process for preparing the same, an intermediate for synthesis of the same and a medicinal composition for bacterially infectious disease therapy containing the same.

  公开了一种β-内酰胺化合物，其表示为式（I）：##STR1##其中，R.sub.1表示酰基；M表示氢原子、保护基或易于在人体内水解的可消除基；B表示由式（b）表示的基团：##STR2##其中，R.sub.2、R.sub.3和R.sub.9中的至少一个表示由式--A--OR.sub.4表示的基团，其中R.sub.4表示氢或较低的烷基基团；A表示具有1到6个碳原子的直链或支链烷基基团；剩余的基团分别独立地表示氢原子、氰基、可以被卤素原子取代的较低烷基基团、可以被较低烷基基团取代的氨基甲酰基团、环烷基团或可以被易于在人体内水解的保护基或可消除基取代的羧基团，当R.sub.9是--A--OR.sub.4时，R.sub.3可以相互结合形成具有3到4个碳原子的烷基基团；Z表示氮原子或由式C--R.sub.10表示的基团，其中R.sub.10表示氢原子、羧基或可以被羟基或较低的烷氧基取代的较低烷基基团，或其药学上可接受的盐，以及制备其的过程、合成其的中间体和用于治疗细菌感染疾病的药物组合物。
• Beta-lactam compound, process for preparing the same, intermediate for synthesis of the same and medicinal composition for bacterially infectious disease therapy containing the same
  申请人：SANKEI PHARMACEUTICAL COMPANY LIMITED

  公开号：EP0302633A2

  公开（公告）日：1989-02-08

  There are disclosed a β-lactam compound represented by the formula (I): wherein R, represents an acyl group; M represents a hydrogen atom, a protective group or an eliminatable group which is easily hydrolyzable in a human body; B represents a group represented by the formula (b): where at least one of R2, R3 and R9 represent a group represented by the formula: -A-OR4 where R4 represents a hydrogen or a lower alkyl group; and A represents a straight or branced alkylene group having 1 to 6 carbon atoms; and a remaining group or groups are each independently a hydrogen atom; a cyano group; a lower alkyl group which may be substituted by a halogen atom; a carbamoyl group which may be substituted by a lower alkyl group; a cycloalkyl group; or a carboxyl group which may be substituted by a protective group or an eliminatable group which is easily hydrolyzable in a human body, and also when Rg is -A-OR4, R2 and R3 may be combined with each other to form an alkylene group having 3 to 4 carbon atoms; and Z represents a nitrogen atom or a group represented by the formula: C-R10 where Rio represents a hydrogen atom, a carboxyl group or a lower alkyl group which may be substituted by a hydroxy group or a lower alkoxy group, or its pharmaceutically acceptable salt, and a process for preparing the same, an intermediate for synthesis of the same and a medicinal composition for bacterially infectious disease therapy containing the same.

  公开了一种由式（I）表示的β-内酰胺化合物： 其中 R 代表酰基；M 代表氢原子、保护基团或在人体内易水解的可消除基团；B 代表由式（b）表示的基团： 其中 R2、R3 和 R9 中至少有一个代表由式表示的基团：-其中 R4 代表氢或低级烷基；A 代表具有 1 至 6 个碳原子的直链或支链亚烷基；其余一个或多个基团各自独立地为氢原子；氰基；可被卤素原子取代的低级烷基；可被低级烷基取代的氨基甲酰基；当 Rg 为-A-OR4 时，R2 和 R3 可相互结合形成具有 3 至 4 个碳原子的亚烷基；Z 代表氮原子或由式表示的基团：C-R10 其中 Rio 代表氢原子、羧基或可被羟基或低级烷氧基取代的低级烷基、 或其药学上可接受的盐，以及制备上述物质、合成上述物质的中间体和含有上述物质的细菌感染性疾病治疗药物组合物的工艺。
• US4987129A
  申请人：——

  公开号：US4987129A

  公开（公告）日：1991-01-22
• US5464617A
  申请人：——

  公开号：US5464617A

  公开（公告）日：1995-11-07